(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Chemical Properties

Melting point:

170-174 °C

alpha 

-46.6 º (c=2, CHCl3 25 ºC)

Boiling point:

317.6±25.0 °C(Predicted)

Density 

1.2486 (rough estimate)

refractive index 

1.5060 (estimate)

Flash point:

170℃

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

-11.75±0.40(Predicted)

form 

Powder

color 

White

optical activity

[α]20/D 44°, c = 2.2 in chloroform

BRN 

6274369

CAS DataBase Reference

104372-31-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

F 

10

HS Code 

29349990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

Reactant involved in:

• Asymmetric synthesis of proton pump inhibitors
• Asymmetric synthesis of polyhydroxylated pyrrolidines
• Diastereoselective hydroxylation of chlorophylls a and b enolate anions

Used in impregnated silica nanoparticles for removal of sulfur mustard from wastewater

Used to modify blebbistatin for investigations of myosin inhibitor design

Uses

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation.

Synthesis

The enantiopure (1S)-(+)-(Camphorylsulfonyl)oxaziridine and (1R)-(-)-(10-Camphorsulfonyl)oxaziridine and [(8,8- dichlorocamphor)sulfonyl]oxaziridines (2) are commercially available. They can also be prepared on a large scale via the oxidation of corresponding camphorsulfonimines with buffered Potassium Monoperoxysulfate (Oxone) or buffered peracetic acid. Since oxidation takes place from the endo face of the C=N double bond, only a single oxaziridine isomer is obtained. The precursor camphorsulfonimines can be prepared in 3 steps (>80% yield) from inexpensive (+)- and (-)-10-Camphorsulfonic Acids. A variety of (camphorylsulfonyl)oxaziridine derivatives such as (2)-(4) are also readily available via the functionalization of the camphorsulfonimines followed by oxidation.

Synthesis

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine is a neutral, aprotic, electrophilic, and asymmetric oxidizing agents for the chemoselective oxidation of many nucleophilic substrates such as sulfides, enamines, enol esters, carbanions, and enolates.

References

1. Mergelsberg, I.; Gala, D.; Scherer, D.; DiBenedetto, D.; Tanner TL 1992, 33, 161.
2. Davis, F. A.; Kumar, A.; Chen, B.-C. JOC 1991, 56, 1143.
3. Chen, B.-C.; Weismiller, M. C.; Davis, F. A.; Boschelli, D.; Empfield, J. R.; Smith, III, A. B. T 1991, 47, 173.

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine(104372-31-8)Related Product Information

• Resin epoxy
• White camphor oil
• (1R)-(-)-10-Camphorsulfonic acid
• 2-Methylcyclohexylamine
• 2-CYCLOPENTYL-ETHYLAMINE
• Cyclopentylamine
• Ethanesulfonamide
• 3-METHYLCYCLOHEXYLAMINE
• BORNYLAMINE
• 2-Ethyl-1-hexanethiol
• (1S)-(+)-(10-CAMPHORSULFONYL)OXAZIRIDINE,(1S)-(+)-(10-Camphorsulfonyl)oxaziridine (1S)-(+)-2,N-Epoxy-exo-10,2-bornanesultam
• Camphor
• DL-Camphor
• EPOXY
• 1-PENTANESULFONAMIDE
• 4-04-00-00045 (Beilstein Handbook Reference)
• 1-HEXANESULFONAMIDE
• PROPANE-1-SULFONAMIDE